A new route towards fimbrolide analogues: importance of the exomethylene motif in LuxR dependent quorum sensing inhibition

A new route towards fimbrolide analogues: importance of the exomethylene motif in LuxR dependent quorum sensing inhibition

Sixteen analogues of fimbrolides (brominated 3-substituted-5-methylene-2(5H)-furanones), naturally occurring bacterial quorum sensing (QS) inhibitors, were synthesized by a novel sequence. The importance of the methylene group, either brominated or non-brominated, in LuxR-dependent QS inhibition was...

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Veröffentlicht in:MedChemComm 2013, Vol.4 (2), p.363-366
Hauptverfasser: Sabbah, Mohamad, Bernollin, Maud, Doutheau, Alain, Soulère, Laurent, Queneau, Yves
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Organic chemistry
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Zusammenfassung:Sixteen analogues of fimbrolides (brominated 3-substituted-5-methylene-2(5H)-furanones), naturally occurring bacterial quorum sensing (QS) inhibitors, were synthesized by a novel sequence. The importance of the methylene group, either brominated or non-brominated, in LuxR-dependent QS inhibition was demonstrated. One of the most active furanone-type QS inhibitors was identified, with an IC50 of 0.6 μM.
ISSN:2040-2503
2040-2511
DOI:10.1039/C2MD20298K